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16th April 2019 @ 14:19

Synthesis of final drug analogue using previously syntheised intermediate Synthesis of 2-chloro-6-(2-hydrazinyl)(4-nitrobenzlidene)pyrazine (SM, RM, 1-1)


Risk assessment 

Nitrobenzaldehyde 2nd reaction.pdf

Reaction scheme

Tabulated quantities

  2-chloro-6-(2-hydrazinyl)(4-nitrobenzlidene)pyrazine  PIDA Product
Mass / mg  20.1 31.0   13.1
Moles / mmol 0.0726  0.0963   0.0475
Equivalents  1.00 1.33 


Yield: 65.6%


Procedure 

Diacetoxyiodobenzene (PIDA) (31.0 mg, 0.0963 mmol) and intermediate 2-chloro-6-(2-hydrazinyl)(4-nitrobenzlidene)pyrazine (20.1 mg 0.0726 mmol) were added to a 50 mL round bottomed flask. The flask was evacuated and placed under nitrogen. Dry DCM (10 mL) was then added. The resulting solution was stirred at room temperature until TLC had shown the reaction had gone to completion. The solvent was removed in vacuo.

Analytical data

 

p3 Assigned .pdf
1H NMR

P3 13C (1).pdf
13C NMR

P3 (1).pdf
IR

Intermediate3.pdf
MS

Write up data

Experiemental completed as shown in procedure, reaction time 180 minutes 

InChi keys

PIDA: ZBIKORITPGTTGI-UHFFFAOYSA-N

2-chloro-6-(2-hydrazinyl)(4-nitrobenzlidene)pyrazine: IEHJAFIAPRDGAK-LHHJGKSTSA-N

5-chloro-3-(3-nitrophenyl)-[1,2,4]triazolo[4,3-a]pyrazine: WCCGFMGKEGZANC-UHFFFAOYSA-N

 

Attached Files
Nitrobenzaldehyde 2nd reaction.pdf
p3 scheme.png
p3 Assigned .pdf
P3 13C (1).pdf
P3 (1).pdf
Intermediate3.pdf